(R)-2-(o-tolyl)propan-1-ol | 1313051-55-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (R)-2-(o-tolyl)propan-1-ol
• 英文别名: (2r)-2-(2-Methylphenyl)propan-1-ol
• CAS: 1313051-55-6
• 化学式: C₁₀H₁₄O
• 分子量: 150.221
• InChiKey: FXHMWNFNIMXBJK-VIFPVBQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  11
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为产物：
  描述：

  邻甲基苯甲酸甲酯 在 甲醇 、 Porcine pancreas lipase type II 、 dimethyl sulfide borane 、 对甲苯磺酸 、 对苯二酚 、 sodium hydroxide 作用下， 以 四氢呋喃 、 乙醚 、 甲基叔丁基醚 、 苯 为溶剂， 反应 6.5h， 生成 (R)-2-(o-tolyl)propan-1-ol
  参考文献：
  名称：

  Lipase-mediated resolution of substituted 2-aryl-propanols: application to the enantioselective synthesis of phenolic sesquiterpenes

  摘要：

  A comprehensive study of the lipase-mediated resolution of substituted 2-aryl-propanols is reported. The latter alcohols were submitted to the irreversible acetylation catalyzed either by PPL, CRL, or lipase PS. The enantioselectivity of these transformations was dependent on the type of lipase used. The type of substituents and particularly their position on the aromatic ring strongly affected the selectivity of the reaction. The experiments described prove that PPL is the more versatile lipase catalyzing the acetylation with an enantiomeric ratio (E) value that ranges from 1 up to 144, depending on the substrate used. Conversely, the same transformations were catalyzed by CRL and lipase PS with an enantiomeric ratio value, which is always less than 5. The remarkable behavior of PPL was exploited in the large scale resolution of some substituted 2-aryl-propanols whose enantiomeric forms are relevant building blocks in the enantioselective synthesis of phenolic sesquiterpenes. By these means, the synthesis of (S)-turmeronol B and the formal syntheses of (R)-curcumene, (R)-curcuphenol, (R)-xanthorrhizol, and (R)-curcuhydroquinone were accomplished. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2011.03.012

文献信息

• Highly Enantioselective Catalytic Kinetic Resolution of α‐Branched Aldehydes through Formal Cycloaddition with Homophthalic Anhydrides
  作者：Umar Farid、Maria Luisa Aiello、Stephen J. Connon

  DOI：10.1002/chem.201902422

  日期：2019.8

  A new catalytic methodology was developed to promote an efficient one‐pot kinetic resolution of racemic aldehydes with selectivity (s*) of up to 91 (99:1 d.r., >99 % ee) in a cycloaddition reaction with enolizable anhydrides to afford dihydroisocoumarin products (a core prevalent in natural products and molecules of medicinal interest) containing three contiguous stereocentres.

  开发了一种新的催化方法，以促进外消旋醛的有效单锅动力学拆分，其选择性（s *）高达91（99：1 dr，> 99％  ee），可与可烯醇化的酸酐进行环加成反应，制得二氢异香豆素产品（在天然产物和药用分子中普遍存在的核心）包含三个连续的立体中心。
• Enantioselective Synthesis of 4-Methyl-3,4-dihydroisocoumarin via Asymmetric Hydroformylation of Styrene Derivatives
  作者：Bo Qu、Renchang Tan、Madison R. Herling、Nizar Haddad、Nelu Grinberg、Marisa C. Kozlowski、Xumu Zhang、Chris H. Senanayake

  DOI：10.1021/acs.joc.8b02813

  日期：2019.4.19

  Enantioenriched aldehydes are produced through asymmetric hydroformylation of styrene derivatives using BIBOP-type ligands. The featured example is enantioselective synthesis of 4-methyl-3,4-dihydroisocoumarin, which was prepared in a 95.1:4.9 enantiomeric ratio from asymmetric hydroformylation of ethyl 2-vinylbenzoate followed by in situ lactonization during the reduction process. The conditions are

  使用BIBOP型配体通过苯乙烯衍生物的不对称加氢甲酰化制得对映体丰富的醛。典型的例子是4-甲基-3,4-二氢异香豆素的对映选择性合成，该合成是通过2-乙烯基苯甲酸乙酯的不对称加氢甲酰化，然后在还原过程中进行原位内酯化而以95.1：4.9的对映体比例制备的。该条件与富电子和贫电子的取代基均相容。
• Easily Accessible TADDOL-Derived Bisphosphonite Ligands: Synthesis and Application in the Asymmetric Hydroformylation of Vinylarenes
  作者：Simon Allmendinger、Hirotaka Kinuta、Bernhard Breit

  DOI：10.1002/adsc.201400657

  日期：2015.1.12

  The synthesis of chiral bidentate bisphosphonite ligands based on the TADDOL motif from readily available starting materials has been developed. Taking advantage of the modular nature of the building blocks, a diverse ligand library has been prepared. Their catalytic potential has been evaluated in the asymmetric hydroformylation of styrene and derivatives. These catalysts showed high activity and

  已经开发了从容易获得的起始原料合成基于TADDOL基序的手性双齿双膦酸酯配体。利用构建模块的模块化性质，已准备了一个多样化的配体库。在苯乙烯及其衍生物的不对称加氢甲酰化反应中，已对它们的催化潜力进行了评估。这些催化剂显示出高活性，并提供了高对映体纯度的醛。